Organic electroluminescent devices, aminostyrylnaphthalene compounds and synthesis intermediates thereof, and production processes of the same

Abstract

An organic electroluminescent device includes an anode, a cathode, and an organic layer having a light-emitting area and arranged between the anode and the cathode. The organic layer contains in at least a part thereof at least one aminostyrylnaphthalene compound represented by the following formula [I], [II] or [III]: wherein R 1 , R 2 , R 11 , R 12 , R 23 and R 24 are each a phenyl or naphthyl group, R 3 , R 4 , R 13 , R 14 , R 25 and R 26 are each an electron attracting group such as a cyano group, and R 5 , R 15 and R 27 are each a substituent group such as an alkyl group.

1. A process for the production of an aminostyrylnaphthalene compound represented by formula [A]: 
       
         
           
           
               
               
           
         
         wherein, 
         R a  and R b  may be the same or different and each independently represents a substituted or unsubstituted aryl group, 
         R c , R d , R e , R g , R h  and R i  may be the same or different, at least one of R c , R d , R e , R g , R h  and R i  independently represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group or a halogen atom, and the remaining one or ones of R c , R d , R e , R g , R h  and R i , if any, are each a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group or a halogen atom, and 
         R f  represents an alkyl selected from the group consisting of methyl, ethyl n-propyl, i-propyl, n-butyl, i-butyl, t-butyl and allyl, a substituted or unsubstituted alicyclic hydrocarbon group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted alicyclic hydrocarbyloxy group or a substituted or unsubstituted aromatic hydrocarbyloxy group; 
         which method comprises subjecting a 4-aminobenzaldehyde represented by the following formula [B] and at least one of a phosphonate ester represented by the following formula [C] and a phosphonium represented by the following formula [D] to condensation: 
       
       
         
           
           
               
               
           
         
         wherein, R a  and R b  have the same meanings as defined above, 
       
       
         
           
           
               
               
           
         
         wherein, R j  represents a hydrocarbon group, R c , R d , R e , R f , R g , R h  and R i  have the same meanings as defined above, and X represents a halogen atom. 
       
     
     
       2. A process for the production of an aminostyrylnaphthalene compound represented by the formula [I], [II] or[III]: 
       
         
           
           
               
               
           
         
         wherein, R 1  and R 2  may be the same or different and each independently represents a phenyl group represented by the following formula (1): 
       
       
         
           
           
               
               
           
         
         wherein, R 6 , R 7 , R 8 , R 9  and R 10  may be the same or different, at least one of R 6  to R 10  represents a hydrogen atom, a saturated or unsaturated hydrocarbon group having at least one carbon atom with a proviso that, when at least two adjacent ones of R 6  to R 10  each represents a saturated or unsaturated hydrocarbon group having at least one carbon atom, at least said two adjacent ones of R 6  to R 10  may be fused together to form a ring, a saturated or unsaturated hydrocarbyloxy group having at least one carbon atom, a saturated or unsaturated hydrocarbylamino group having at least one carbon atom, a trifluoromethyl group, a cyano group or a halogen atom, and the remaining one or ones of R 6  to R 10 , if any, are each a hydrogen atom, a saturated or unsaturated hydrocarbon group having at least one carbon atom with a proviso that, when at least two adjacent ones of R 6  to R 10  each represents a saturated or unsaturated hydrocarbon group having at least one carbon atom, at least said two adjacent ones of R 6  to R 10  may be fused together to form a ring, a saturated or unsaturated hydrocarbyloxy group having at least one carbon atom, a saturated or unsaturated hydrocarbylamino group having at least one carbon atom, a trifluoromethyl group, a cyano group or a halogen atom, 
         R 3  and R 4  may be the same or different, one of R 3  and R 4  represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group or a halogen atom, and the remaining one represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group or a halogen atom, and 
         R 5  represents an alkyl selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, and allyl, a substituted or unsubstituted, alicyclic hydrocarbon group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted, alicyclic hydrocarbyloxy group, or a substituted or unsubstituted, aromatic hydrocarbyloxy group, 
       
       
         
           
           
               
               
           
         
         wherein, R 11  and R 12  may be the same or different and each independently represents a naphthyl group represented by the following formula (2): 
       
       
         
           
           
               
               
           
         
         wherein R 16 , R 17 , R 18 , R 19 , R 20 , R 21  and R 22  maybe the same or different, at least one of R 16  to R 22  represents a hydrogen atom, a saturated or unsaturated hydrocarbon group haying at least one carbon atom, a saturated or unsaturated hydrocarbyloxy group having at least one carbon atom, a saturated or unsaturated hydrocarbylamino group having at least one carbon atom, a trifluoromethyl group, a cyano group or a halogen atom, and the remaining one or ones of R 16  to R 22 , if any, are each a hydrogen atom, a saturated or unsaturated hydrocarbon group having at least one carbon atom, a saturated or unsaturated hydrocarbyloxy group having at least one carbon atom, a saturated or unsaturated hydrocarbylamino group having at least one carbon atom, a trifluoromethyl group, a cyano group or a halogen atom, 
         R 13  and R 14  may be the same or different, one of R 13  and R 14  represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group or a halogen atom, and the remaining one represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group or a halogen atom, and 
         R 15  represents an alkyl selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, and allyl, a substituted or unsubstituted, alicyclic hydrocarbon group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted, alicyclic hydrocarbyloxy group, or a substituted or unsubstituted, aromatic hydrocarbyloxy group, 
       
       
         
           
           
               
               
           
         
         wherein, R 23  is a phenyl group represented by the following formula (3): 
       
       
         
           
           
               
               
           
         
         wherein, R 28 , R 29 , R 30 , R 31  and R 32  may be the same or different, at least one of R 28  to R 32  represents a hydrogen atom, a saturated or unsaturated hydrocarbon group having at least one carbon atom with a proviso that, when at least two adjacent ones of R 28  to R 31  each represents a saturated or unsaturated hydrocarbon group having at least one carbon atom, at least said two adjacent ones of R 28  to R 32  may be fused together to form a ring, a hydrocarbyloxy group having at least one carbon atom, a hydrocarbylamino group having at least one carbon atom, a trifluoromethyl group, a cyano group or a halogen atom, and the remaining one or ones of R 28  to R 32 , if any, are each a hydrogen atom, a saturated or unsaturated hydrocarbon group having at least one carbon atom with a proviso that, when at least two adjacent ones of R 28  to R 32  each represents a saturated or unsaturated hydrocarbon group having at least one carbon atom, at least said two adjacent ones of R 28  to R 32  may be fused together to form a ring, a saturated or unsaturated hydrocarbyloxy group having at least one carbon atom, a saturated or unsaturated hydrocarbylamino group having at least one carbon atom, a trifluoromethyl group, a cyano group or a halogen atom, 
         R 24  represents a naphthyl group represented by the following formula (4): 
       
       
         
           
           
               
               
           
         
         wherein, R 33 , R 34 , R 35 , R 36 , R 37 , R 38  and R 39  may be the same or different, at least one of R 33  to R 39  represents a hydrogen atom, a saturated or unsaturated hydrocarbon group having at least one carbon atom, a saturated or unsaturated hydrocarbyloxy group having at least one carbon atom, a saturated or unsaturated hydrocarbylamino group having at least one carbon atom, a trifluoromethyl group, a cyano group or a halogen atom, and the remaining one or ones of R 33  to R 39 , if any, are each a hydrogen atom, a saturated or unsaturated hydrocarbon group having at least one carbon atom, a saturated or unsaturated hydrocarbyloxy group having at least one carbon atom, a saturated or unsaturated hydrocarbylamino group having at least one carbon atom, a trifluoromethyl group, a cyano group or a halogen atom, 
         R 25  and R 26  may be the same or different, one of R 25  and R 26  represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group or a halogen atom, and the remaining one represents a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group or a halogen atom, and 
         R 27  represents an alkyl selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, n-butyl and allyl, a substituted or unsubstituted, alicyclic hydrocarbon group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted, alicyclic hydrocarbyloxy group, or a substituted or unsubstituted, aromatic hydrocarbyloxy group; 
         which method comprises subjecting a 4-(N,N-diarylamino)benzaldehyde represented by the following formula [IV] and at least one of a phosphonate ester represented by the following formula [V] and a phosphonium represented by the following formula [VI] to condensation: 
       
       
         
           
           
               
               
           
         
         wherein, R 71  and R 72  each independently represents an aryl group corresponding to R 1 , R 2 , R 11 , R 12 , R 23  or R 24  as defined above, 
       
       
         
           
           
               
               
           
         
         wherein, R 73  represents a hydrocarbon group, R 74  and R 75  each independently represents a group corresponding to R 3 , R 4 , R 13 , R 14 , R 25  or R 76  as defined above, R 76  represents a group corresponding to R 5 , R 15  or R 27  as defined above, and X represents a halogen atom. 
       
     
     
       3. The process according to  claim 1 , wherein said condensation is conducted by the Wittig-Horner reaction, at least one of said phosphonate ester and said phosphonium is treated with a base in a solvent to form carbanions, and said carbanions and said 4-(N,N-diarylamino)benzaldehyde are subjected to condensation. 
     
     
       4. The process according to  claim 1 , wherein said condensation is conducted by the Wittig reaction, at least one of said phosphonate ester and said phosphonium is treated with a base in a solvent to form carbanions, and said carbanions and said 4-(N,N-diarylamino)benzaldehyde are subjected to condensation. 
     
     
       5. The process according to  claim 2 , wherein the aminostyrylnaphthalene compound is represented by one of the formula (5), (6), (7), (8), (9), (10), (11), (12), (13), (14), (15), (16) or (17): 
       
         
           
           
               
               
           
         
         wherein R 40  represents a saturated or unsaturated alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group, and R 41  has the same meaning as R 5 , 
       
       
         
           
           
               
               
           
         
         wherein R 42  and R 43  may be the same or different and each independently represents a saturated or unsaturated alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group, and R 44  has the same meaning as R 5 , 
       
       
         
           
           
               
               
           
         
         wherein R 45  represents a saturated or unsaturated alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group, and R 46  has the same meaning as R 27 , 
       
       
         
           
           
               
               
           
         
         wherein R 47  and R 48  may be the same or different, one of R 47  and R 48  represents a saturated or unsaturated alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group, the remaining one of R 45  and R 48  represents a saturated or unsaturated alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group, and R 49  has the same meaning as R 27 , 
       
       
         
           
           
               
               
           
         
         wherein R 50  represents a saturated or unsaturated alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group, and R 51  has the same meaning as R 27 , 
       
       
         
           
           
               
               
           
         
         wherein R 52  and R 53  may be the same or different, one of R 52  and R 53  represents a saturated or unsaturated alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group, the remaining one of R 52  and R 53  represents a saturated or unsaturated alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group, and R 54  has the same meaning as R 27 , 
       
       
         
           
           
               
               
           
         
         wherein R 55  represents a saturated or unsaturated alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group, and R 56  has the same meaning as R 5 , 
       
       
         
           
           
               
               
           
         
         wherein R 57  represents a saturated or unsaturated alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group, and R 58  has the same meaning as R 5 , 
       
       
         
           
           
               
               
           
         
         wherein R 59  represents a saturated or unsaturated alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group, and R 60  has the same meaning as R 5 , 
       
       
         
           
           
               
               
           
         
         wherein R 61  represents a saturated or unsaturated alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group, and R 62  has the same meaning as R 15 , 
       
       
         
           
           
               
               
           
         
         wherein R 63  and R 64  may be the same or different, one of R 63  and R 64  represents a saturated or unsaturated alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group, the remaining one of R 63  and R 64  represents a saturated or unsaturated alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group, and R 65  has the same meaning as R 15 , 
       
       
         
           
           
               
               
           
         
         wherein R 66  represents a saturated or unsaturated alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group, and R 67  has the same meaning as R 15 , 
       
       
         
           
           
               
               
           
         
         wherein R 68  and R 69  may be the same or different, one of R 68  and R 69  represents a saturated or unsaturated alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group, the remaining one of R 68  and R 69  represents a saturated or unsaturated alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group, and R 70  has the same meaning as R 15 .